35951-28-1Relevant articles and documents
Sharpless,Teranishi
, p. 185 (1973)
A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant
Tang, Shi-Zhong,Zhao, Wenshuang,Chen, Tao,Liu, Yang,Zhang, Xiao-Ming,Zhang, Fu-Min
supporting information, p. 4177 - 4183 (2017/12/18)
α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).
Addition of NOCl to cyclic vinylsilanes: An unexpected reversal of regiochemistry
Mallya, M. Narendra,Nagendrappa, Gopalpur,Shashidhara Prasad,Sridhar,Lokanath,Begum
, p. 2565 - 2568 (2007/10/03)
NOCl adds to cyclic vinylsilanes in a syn manner with NO+ bonding to the β-carbon and Cl- to the α-carbon, which is a reversal of the regiochemistry expected from the β-silicon effect. The adducts dimerize to a single diastereomer containing enantiomeric pairs and/or give secondary products on further reaction.
